3-Azidopropionic acid

The first application of copper(I)-catalyzed 1,3-dipolar cycloaddition in preparation of [18F]fluoropeptides was reported by Marik and Sutcliffe in 2006 (Figure 14.9) [92]. Three [18F]fluoroalkynes (n = 1, 2, and 3) were prepared in yields ranging from 36% to 80% by nucleophilic substitution of a p-toluenesulfonyl moiety with [18F]fluoride ion. Reaction of these [18F]fluoroalkynes with various peptides (previously derivatized with 3-azidopropionic acid) via the Cu(I)-mediated 1,3-dipolar cycloaddition provided the desired 18F-labeled peptides in 10 minutes at room temperature with yields of 54-99% and great radiochemical purity (81-99%) [82]. 

Azidopropionic Acid Ami do. See under Propionic Acid Amide and Beil 2, 263-4 (114)... 

Azidopropionic Acid, Methyl Ester. See under Propionic Acid and J.H.Boyer, JACS 73, 5248-52(1951) CA 47, 489-90(1953)... 

Figure 9A. Optical rotatory dispersion (1) and absorption spectrum (2) of a-azidopropionic acid dimcthylamidc in ether. Curve 3 the rotatory contribution of the azido group.

The derivatives of a-azidopropionic acid were employed by Kuhn in his pioneering research on o.r.d. and c.d. Figure 9 (adapted from a review paper by Kuhn ) shows the absorption band of a-azidopropionic acid dimethylamide, its c.d. spectrum and the contribution of N3 to its molecular rotatory power ([ ]). 

Azidopropionic acid.. (+)Chloropropionic acid. (+)Bromopropionic acid. (+)Iodopropionic acid... 

Ethyl (R)-2-azidopropionate Propanoic acid, 2-azido-, ethyl ester, (R)- (12) (124988-44-9)... 

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